Regio- and Stereoselective Alkylation of Pyridine-N-oxides: Synthesis of Substituted Piperidines and Pyridines

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• 作者：Deepak Kumar Barange ; Magnus T. JohnsonAndrew G. Cairns ; Roger Olsson ; Fredrik Almqvist
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：December 16, 2016
• 年：2016
• 卷：18
• 期：24
• 页码：6228-6231
• 全文大小：442K
• ISSN：1523-7052

文摘

Regio- and stereoselective addition of alkyl Grignard reagents to pyridine-N-oxides gave C2-alkylated N-hydroxy-1,2,5,6-tetrahydropyridines and trans-2,3-disubstituted N-hydroxy-1,2,5,6-tetrahydropyridines in good to excellent yields. These intermediates were aromatized or alternatively reduced in one-pot methodologies for efficient syntheses of alkylpyridines or piperidines, respectively. These reactions have a broad substrate scope and short reaction times.